Should race be considered one of the criteria for acceptance into U.S. schools? That’s the questions that is confronting President Trump and Education Secretary Betsy Devos as they examine Obama-era guidelines that allow for schools to enforce “race quotas” in the admissions selection process.

On the one hand, Obama-era policies were enacted primarily to encourage an atmosphere of diversity and multiculturalism within the nation’s school system. On the other hand, critics of this policy have argued that hard quota limits have unfairly discriminated against otherwise worthy candidates, creating the very system of inequality that the law was trying to abolish in the first place.

The first president to recognize this discrepancy was President John F. Kennedy, who wrote an executive order nearly sixty years ago recognizing the disadvantages for women and minorities and taking steps to enact it. Since then, policies have shifted slightly since then as to how the law is to be interpreted, primarily wavering with the party lines.

One of the premier cases in the country that deals with this very issue deals with a case that Asian-Americans have brought before Ivy League school Harvard University, who the students claim have unfairly excluded from admission in an effort to keep slots open for other minority-based students. With a fast track to the Supreme Court, it’s inevitable that the case will be heard by the highest legal minds in the land.

Throwing another wrench into this equation is the imminent retirement of Court Justice Anthony Kennedy – a moderate on several issues who has acted as a swing vote in some of the nation’s biggest cases. He argued for schools being able to use race as one of the criteria for enrollment in 2016’s Fisher vs. The University of Texas at Austin. The case revolved around a white woman who claimed she was denied admission to the university because of her race. Kennedy wrote in his follow-up brief that it remains an “enduring challenge” to reconcile “the pursuit of diversity with the constitutional promise of equal treatment and dignity.”

Surely this is the case facing Trump, who remains steadfast in his desire to see race-based admission standards lifting, favoring Bush Jr. policies over those found in the Obama-era. So far, nothing he has done has been lawfully-binding, but it remains yet to be seen how he will proceed with this sticky issue moving forward.